I could help if you describe what step you are having problems with.
Yes, you can upload whole folder or set of files using WinSCP at once.
For general help on uploading, please see
https://winscp.net/eng/docs/task_upload_________________Martin Prikryl

I could help if you describe what step you are having problems with.
Yes, you can upload whole folder or set of files using WinSCP at once.
For general help on uploading, please see
https://winscp.net/eng/docs/task_upload

I want to upload only the .htm files (not the jpg, pdf, ... etc.) and I'd like to do all the htm files on all directors from the top directory down.

The way I've done this in the past is to go into each directory (several dozen of them), sort the files by type (so all the htms are lumped together), select all the htms, and copy them to the server panel. Seems like there must be a better way?